1,3-Propanediol → 6-Bromo-3-(4-methoxyphenyl)imidazo[1,2-a]pyridine

HRID 1792429Notes

Reaction equation

HRID 1792429 reaction equation
C(O)CCO.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.[Br:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:24](I)=[CH:25][N:26]=2)[CH:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)C.CN(C)C=O>[Br:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:24]([C:11]3[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=3)=[CH:25][N:26]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 62657Potassium Phosphate, TribasicHCID 201262(4-Methoxyphenyl)boronic acidHCID 220316326-Bromo-3-iodoimidazo(1,2-a)pyridine

Product 1

HCID 220314586-Bromo-3-(4-methoxyphenyl)imidazo[1,2-a]pyridineYield 78.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

0.81 mL 1,3-propane diol was added to a suspension of 1.69 g 4-methoxyphenylboronic acid in 15 mL diethyl ether, and the mixture was stirred a room temperature for 1 hour. Formed water was removed, and the organic solvent was evaporated, whereby an oil was obtained. 2.7 g 6-bromo-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 49), 3.5 g potassium phosphate, 483 mg tetrakistriphenyl phosphine palladium and 40 mL N,N-dimethylformamide were added thereto and heated at 90° C. for 3 hours under nitrogen atmosphere. Insolubles were filtered off, the solvent was removed, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give 2 g of the title compound as an oil.

Workup

  1. customFormed water was removed
  2. customthe organic solvent was evaporated
  3. customwhereby an oil was obtained
  4. temperatureheated at 90° C. for 3 hours under nitrogen atmosphere
  5. filtrationInsolubles were filtered off
  6. customthe solvent was removed
  7. customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bdd0da86c2d84590b4e49a37136c4830
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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